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There had been autograph cards before Fleer Skybox issued "Star Trek The Original Series 1966-1967 Season One" in 1997, but they had usually been ultra-rare chase cards with extremely high odds.  TOS Season One was the first set to offer the guarantee of "One Autograph Card Per Box"!
Of course, some autographs were harder to get than others, but if you are lucky you CAN get a complete set of the Main Stars from the show (over the three sets which offered autograph cards) and there were better odds of getting some of the more interesting 'Guest Stars'!
This is the only series (at time of writing) that I haven't got the Captain's autographed card from.  I'm working on it though...

In 2001, Rittenhouse Archive took over the TOS card licence and, in 2002, issued a set to mark the 35th anniversary of the show.

PLEASE NOTE:  This page contains a lot of pictures, which may well take some time to load up.  Please be patient and, if things seem to have got stuck, hit 'Refresh' or the equivalent! IMPORTANT NOTE: Copyright exists in all the images on this page.  My use of these images does not, and should not be considered to, indicate the approval of the relevant copyright holders.
Should said copyright holders require me to remove these images, I will willingly do so.
Main Cast Autographs Leonard Nimoy as 'Mr Spock' (A59) James Doohan as 'Scotty' (A60) Nichelle Nichols as 'Lt. Uhura' (A34) George Takei as 'Lt. Sulu' (A33)
Leonard Nimoy
James Doohan Nichelle Nichols George Takei
Walter Koenig as 'Ensign Checkov' (A28) Grace Lee Whitney as 'Yeoman Rand' (A5) I'm working on getting a set of all 9 'main' cast member autographs from this set; all I need are William Shatner, DeForest Kelley and Majel Barrett.  The only thing stopping me is money!!!  If I ever get them, they'll appear here.
Walter Koenig Grace Lee Whitney
Captains Card C1 (Front) - 783/1200 Captains Card C1 (Back) - 783/1200 The Season Three set had a 'Captains Card' which was part of a set of four cards issued in 1998/1999. (the others were to be found in "TNG Season Seven", "DS9 Memories From the Future" and "VGR Profiles")  Each card was limited to 1200 (odds - 1:750) and was hand numbered on the back
This one shows Captain James T. Kirk and is numbered '783/1200'
Fleer Skybox
Season One  Robert Justman - Associate Producer (A6) William Campbell as 'Trelane' (A15) Bruce Hyde as 'Lt. Kevin Riley' (A14) D.C.Fontana - Writer (A29)
Robert Justman (Associate Producer)
William Campbell (Trelane) Bruce Hyde (Lt. Kevin Riley); my first ever trading card! D.C.Fontana (Writer)
Season Two John Fiedler as 'Hengist' (A40) Charles Macaulay as 'Jaris' (A41) Charlie Brill as 'Arne Darvin' (A44) William Campbell as 'Koloth' (A45)
John Fiedler (Hengist) Charles Macaulay (Jaris) Charlie Brill (Arne Darvin) William Campbell (Koloth)
Nancy Kovack as 'Nona' (A49) Joseph Ruskin as 'Galt' (A50) Anthony Caruso as 'Bela Oxmyx' (A52) Le Delano as 'Kalo' (A53)
Nancy Kovack (Nona - my first autograph card actually 'pulled' from a pack!) Joseph Ruskin (Galt) Anthony Caruso (Bela Oxmyx) Lee Delano (Kalo)
Warren Stevens as 'Rojan' (A55)
Teri Garr as 'Roberta Lincoln' (A58)
Warren Stevens (Rojan) Teri Garr (Roberta Lincoln)
Season Three Herb Solow - Executive in Charge of Production (A64) Walter M. Matt Jeffries - Art Director (A65) Ron Soble as 'Wyatt Earp' (A66) Diana Muldaur as 'Dr Miranda Jones' (A70)
Herb Solow (Executive in Charge of Production) Walter M 'Matt' Jeffries (Art Director, after whom the "Jeffries Tubes" were named!) Ron Soble (Wyatt Earp) Diana Muldur (Dr Miranda Jones)
Michael Ansara as 'Kang' (A72)
Frank Gorshin as 'Bele' (A77) Sharon Acker as 'Odona' (A79) Victor Brandt as 'Tongo Rad' (A82)
Michael Ansara (Kang) Frank Gorshin (Bele) Sharon Acker (Odona) Victor Brandt (Tongo Rad)
Nathan Jung as 'Genghis Khan' (A84)
Nathan Jung (Genghis Khan)
One Man, Three Cards - The Three Faces of William Campbell!
William Campbell as 'Trelane' (A15) William Campbell as 'Koloth' (A45) William Campbell as 'Koloth' (A10)
'The Squire of Gothos' (Season One) 'Koloth' (Season Two) 'Koloth' (DS9 Memories from the Future)
A
Rittenhouse Archive
35th Anniversary (2002) Willaim Shatner as 'Captain James Kirk' and Leonard Nimoy as 'Spock' In 2002, Rittenhouse Archive released a special set to mark the 35th Anniversary of Star Trek.  This set, in the HoloFex format unique to Rittenhouse (the cards were printed on a 'holofoil' type card) included three autographs, from Trek personalities who had not previously signed for trading cards, in every box of 24 packs - each pack contained six cards.
There was one extra special auto card with two autographs - William Shatner and Leonard Nimoy!  Limited to 500 (Odds 1:480)
DA1
Joanne Linville as 'Romulan Commander'  in 'The Enterprise Incident' (A1) Sally Kellerman as 'Dr. Dehner' in 'Where No Man Has Gone Before' (A5) Paul Comi as 'Lt. Stiles' in 'Balance of Terror' (A10) Celeste Yarnall as 'Yeoman Landon' in 'The Apple' (A16)
Joanne Linville (Romulan Commander) Sally Kellerman (Dr. Dehner) Paul Comi (Lt. Stiles) Celeste Yarnall (Yeoman Landon)
William Smithers as 'Merrick' in 'Bread and Circuses' (A27) Louise Sorel as 'Rayna Kapec' in 'Requem For Methuselah' (A28) Jan Shutan as 'Lt. Mira Romaine' in 'The Lights of Zetar' (A29) Alexander Courage - Composer 'Star Trek Theme' (A31)
William Smithers (Merrick) Louise Sorel (Rayna Kapec) Jan Shutan (Lt. Mira Romaine) Alexander Courage (Composer of the Star Trek theme music)
'SketchaFex'(tm) SketchaFex (tm) 'USS Enterprise' (Chris Bolson) SketchaFex (tm) - Back of card SketchaFex (tm) 'Mirror Mirror Spock' (John Czop) There were a variety of these cards, randomly inserted into packs.  The cards were hand-drawn sketches of characters and things from Star Trek - being hand-drawn, each one was slightly different!
"USS Enterprise" drawn by Chris Bolson the back of the SketchaFex(tm) cards "Mirror Mirror Spock" drawn by artist John Czop.
FilmCard 'Federation Foe - Kor' (FF1) A set of 6 cards, again randomly inserted into packs, which contained a film cel (the dark bit in the middle of the card) showing one of the 'villans' from the show.  Unfortunately, I don't have a transparency scanner, so I can't (yet) scan the film cel!
"Federation Foe" film card - Kor (FF1)
The Complete Animated Adventures (2003) Nichelle Nichols (A4)
Nichelle Nichols (Lt. Uhura)
IW1

Instant Win card IW1 - there is a story about this!
The IW2 (right) was sent to Rittenhouse Archives, and they duly sent out the matching SeriCel - which promptly got lost in the postal system.  RA subsequently (and very generously) sent out a replacement - and also sent out the SeriCel for IW1 with the matching cards!
Clicking on the above images should take you to scans of the actual SeriCels - apologies for the scan quality; they are larger than the A4 flatbed scanner I currently own and so I had to 'stitch' two scans together! (takes you to an external webpage)
Instant Win card IW2
Inserted at odds of 1:480, this card entitles the holder to a limited edition Sericel from the Animated Series.
Each card is hand numbered to 250 (this one is 72/250) and embossed - there are two different Sericels to win, making a total of 500 cards.
Quotable Star Trek (2004) Eddie Paskey as 'Lieutenant Leslie' (A101) Lawrence Montaigne as 'Stonn' (A105) In 2004, RA released a set consisting of the most quotable parts of the original series - this featured autographs and saw the return of the card design originally used in the Fleer Skybox sets issued in 1997/8
Eddie Paskey (Lieutenant Leslie) Lawrence Montaigne (Stonn) from "Amok Time"
Star Trek 40 (2006) C6 To mark the 40th anniversary of Star Trek, Rittenhouse Archive released a set covering all 5 series and the movies; included in the set were "From The Archive" costume cards containing pieces of various costumes used in the 40 years of Trek.  This card is the only pack inserted card to contain TWO pieces - one from Sulu's shirt and one from his trousers... (See the TNG page for another card from this set)
C6
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Paul Bines Autograph Card... Only Joking!